1-Methyl-4-piperidone → 6-bromo-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 717793ノート

反応式

HRID 717793 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9]N.[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1>OS(O)(=O)=O.O1CCOCC1>[Br:1][C:2]1[C:3]2[NH:9][C:15]3[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][C:14]=3[C:4]=2[CH:5]=[C:6]([CH3:8])[CH:7]=1

参加物

5

反応物 2

HCID 740491-Methyl-4-piperidoneHCID 292001(2-Bromo-4-methylphenyl)hydrazine

生成物 1

HCID 673765326-bromo-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole収率 69.6%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

(2-Bromo-4-methylphenyl)hydrazine (21.5 g, 0.107 mol) and 1-methylpiperidin-4-one (12.5 mL, 0.107 mol) was dissolved in 7% H2SO4 in 1,4-dioxane (150 mL) and stirred at 80° C. for 90 min. The reaction was monitored by TLC. After completion of the reaction, the dioxane was evaporated under reduced pressure, and the residue basified with aq. NaHCO3 solution, and extracted with EtOAc. The organic layer was evaporated under reduced pressure. The crude product was crystallized from hexane and diethyl ether to afford 20.8 g of 6-bromo-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3) d (ppm): 10.9 (s, 1H), 7.20 (s, 1H), 7.10 (s, 1H), 3.50 (s, 2H), 2.90-2.80 (t, 2H), 2.70-2.60 (t, 2H), 2.40 (s, 3H), 2.30 (s, 3H).

後処理

  1. customAfter completion of the reaction
  2. customthe dioxane was evaporated under reduced pressure
  3. extractionextracted with EtOAc
  4. customThe organic layer was evaporated under reduced pressure
  5. customThe crude product was crystallized from hexane and diethyl ether

出典と根拠

ORDレコード
ord-c74d18c94e3148159f62eb2521398fad
出典データセット
uspto-grants-2015_11
特許番号
US09193728B2

反応ノート

読み込み中…